CS195217B1 - 1,4-Dlalkyl-I.A-palladonium-bicycloEZ.ZrZLctanedibromides and process for their preparation - Google Patents
1,4-Dlalkyl-I.A-palladonium-bicycloEZ.ZrZLctanedibromides and process for their preparation Download PDFInfo
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Abstract
Vynález sa týká 1,4-dialky1-1,4-diazónium· bicyklo[2,2,2]oktándibromidov obecného vzorca * Rl_®N^N®-R22Br® \_7 z a sposobu ich výroby, kde a R2 značí alkylový reíazec s počtom atómov uhlíka 6 až 16 a íj a R2 možu mař rovnaký alebo rSzný význam. Ako je známe, niektoré organické amóniové soli s dlhým alkylovým reíazcom vykazujú letálne účinky na mikroorganizmy. Preto sa používajú ako dezinfekčné prostriedky. U zlúčenin, ktoré sú predmetom vynálezu, sa zistili doteraz neznáme účinky na niektoré mikrobiálně kmene. Pri zrovnaní a komerčnýmí preparátmi tohoto typu používanými v súčasnosti v CSSR, sa zistila podstatné vyššia účinnost predóvšetkým na rezistentné gramnegatívne mikroorganizmy. Uvedené zlúčeniny,sa pripravujú spósobom podlá vynálezu, ktorého podstatou je, že sa nechá zreagovat brómalkán s 1,4-diazabicyklo[2,2,2joktánom v prostředí metylkyanidu pri teplote varu počas 4 hodinThe invention relates to 1,4-dialkyl-1,4-diazonium bicyclo[2,2,2]octane dibromides of the general formula * R1_®N^N®-R22Br® \_7 z and the method of their production, where R2 denotes an alkyl chain with the number of carbon atoms from 6 to 16 and R2 and R2 can have the same or different meanings. As we know, some organic ammonium salts with a long alkyl chain show lethal effects on microorganisms. That is why they are used as disinfectants. The compounds that are the subject of the invention have been found to have hitherto unknown effects on some microbial strains. When compared with commercial preparations of this type currently used in the CSSR, a significantly higher efficiency was found, especially against resistant gram-negative microorganisms. The mentioned compounds are prepared by the method according to the invention, the essence of which is that bromoalkane is allowed to react with 1,4-diazabicyclo[2,2,2octane in methyl cyanide at boiling temperature for 4 hours
Description
Vynález sa týká 1,4-dialky1-1,4-diazónium· bicyklo[2,2,2]oktándibromidov obecného vzorca * Rl_®N^N®-R22Br® \_7 z a sposobu ich výroby, kde a R2 značí alkylový reíazec s počtom atómov uhlíka 6 až 16 a íj a R2 možu mař rovnaký alebo rSzný význam. Ako je známe, niektoré organické amóniové soli s dlhým alkylovým reíazcom vykazujú letálne účinky na mikroorganizmy. Preto sa používajú ako dezinfekčné prostriedky. U zlúčenin, ktoré sú predmetom vynálezu, sa zistili doteraz neznáme účinky na niektoré mikrobiálně kmene.The invention relates to 1,4-diazonium · dialky1-1,4-bicyclo [2.2.2] oktándibromidov of the formula R * _® N ^ N ⊕ -R 2 2Br® \ _7 of a process for their preparation, and wherein R 2 denotes an alkyl chain having a carbon number of 6 to 16 and R 1 and R 2 may have the same or different meanings. As is known, some long-chain organic ammonium salts show lethal effects on microorganisms. They are therefore used as disinfectants. The compounds of the invention have previously been found to have unknown effects on some microbial strains.
Pri zrovnaní a komerčnýmí preparátmi tohoto typu používanými v súčasnosti v CSSR, sa zistila podstatné vyššia účinnost predóvšetkým na rezistentné gramnegatívne mikroorganizmy. Uvedené zlúčeniny,sa pripravujú spósobom podlá vynálezu, ktorého podstatou je, že sa nechá zreagovat brómalkán s 1,4-diazabicyklo[2,2,2joktánom v prostředí metylkyanidu pri teplote varu počas 4 hodin.In comparison and commercial preparations of this type currently used in CSSR, a significantly higher efficacy has been found, in particular to resistant gram-negative microorganisms. The compounds are prepared according to the process of the invention, which comprises reacting the bromoalkane with 1,4-diazabicyclo [2.2.2] octane in methyl cyanide at reflux for 4 hours.
PřikladlEXAMPLE
K 11,2 g /0,1 mol/ 1,4-diazabicyklo[2,2,2]okt ánu rozpuštěného v bezvodom metyl· kyanide /30 ml/ sa přidá 33,0 g /0,2 mol/ 1-brómhexánu a zmes sa zahrieva pod spatným tokom 4 hodiny. Po ukončení reakcie sa rozpúšíadlo oddestiluje za zníženého tlaku a pevný surový produkt sa prekryštalizuje zo zmesi suchého acetonu a metanolu /10:1/. T. t. 1,4-áihexyl-1,4-diazóniumhicyklo[2,2,2Joktándibromidu je 278 až 279 °C, výťažok 86 7°, Rp = 0,78.To 11.2 g (0.1 mol) of 1,4-diazabicyclo [2.2.2] octane dissolved in anhydrous methyl cyanide (30 ml) is added 33.0 g (0.2 mol) of 1-bromohexane and the mixture was heated under reflux for 4 hours. After completion of the reaction, the solvent was distilled off under reduced pressure, and the solid crude product was recrystallized from dry acetone / methanol (10: 1). T. t. 1,4-ahexyl-1,4-diazoniumhicyclo [2.2.2] octanedibromide is 278-279 ° C, yield 867 °, R p = 0.78.
Príkla-d 2Example 2
Pracovný postup je obdobný fako v prítlade 1·, .namiesto _ 1-brómhexánu sa na alkyláciu použil 1-brómdekán. T. t. 1,4-didecyl -1,4-diazóniumbicyklo L2,2,2joktándibromidu je 299 až 301 °C, výčažok 87 %, Rp = 0,61. Příklad 3The procedure is similar to that in Example 1, instead of 1-bromohexane, 1-bromodecane was used for the alkylation. T. t. 1,4-didecyl-1,4-diazoniabicyclo L2,2,2joktándibromidu is 299 to 301 DEG C., yield = 87%, R p = 0.61. Example 3
Pracovný postup je podobný ako v příklade 1, namiesto 1-brómhexánu sado reakcíe použil 1-hrómdodekán. T. t. 1,4-didodecyl-1,4~diazóniumbicyklo[2,2,2]oktándibromidu je 290 až 291 °C, výťažok 89 7ít Ry = 0,39.The procedure is similar to Example 1, using 1-bromododecane instead of 1-bromohexane in the reaction. T. t. 1,4-di-1,4-diazoniabicyclo [2.2.2] oktándibromidu is 290-291 ° C, yield 89 T 7 R R y = 0.39.
Všetky takto připravené zlúčeniny sú hiéle kryštalické látky, rozpustné v polárných, nerozpustné v nepolárných rozpúší-adlách. Teploty topenia sú nekorigované, sústava.pre tenkovrstevnú chromatografiu bóla aceton - 1N HC1 /10:1/. Detekcia Dragendorfovým činidlom - Muniérova modifikácia.All the compounds thus prepared are hi-crystalline substances, soluble in polar, insoluble in non-polar solvents. Melting points are uncorrected, for thin-layer chromatography, acetone-1N HCl (10: 1). Dragendorf reagent detection - Munier modification.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS235878A CS195217B1 (en) | 1978-04-11 | 1978-04-11 | 1,4-Dlalkyl-I.A-palladonium-bicycloEZ.ZrZLctanedibromides and process for their preparation |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS235878A CS195217B1 (en) | 1978-04-11 | 1978-04-11 | 1,4-Dlalkyl-I.A-palladonium-bicycloEZ.ZrZLctanedibromides and process for their preparation |
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| CS195217B1 true CS195217B1 (en) | 1980-01-31 |
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| Application Number | Title | Priority Date | Filing Date |
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| CS235878A CS195217B1 (en) | 1978-04-11 | 1978-04-11 | 1,4-Dlalkyl-I.A-palladonium-bicycloEZ.ZrZLctanedibromides and process for their preparation |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010502613A (en) * | 2006-08-30 | 2010-01-28 | リサーチ ファウンデーション オブ シティ ユニバーシティ オブ ニューヨーク | Antibacterial composition |
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1978
- 1978-04-11 CS CS235878A patent/CS195217B1/en unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010502613A (en) * | 2006-08-30 | 2010-01-28 | リサーチ ファウンデーション オブ シティ ユニバーシティ オブ ニューヨーク | Antibacterial composition |
| EP2061445A4 (en) * | 2006-08-30 | 2011-07-06 | Univ City New York Res Found | ANTIMICROBIAL COMPOSITIONS |
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